HU199062B - Process for steeping seeds with synergetic mixture of copper-oxyquinolate and 5-/phenyl-carbamoyl/-1,3-thiazol derivatives - Google Patents

Abstract

57 The invention relates to fungicidal compositions comprising copper oxyquinolate in combination with certain thiazoles which are applied as seed dressing and intended to prevent fungal attack on seeds.

Description

The present invention relates to a seed dressing process for controlling fungal infestation of seeds.

In the process of the present invention, copper oxyquinolate (Rye (II) complex of 8-hydroxyquinoline) and 5- (phenylcarbamoyl) -1,3-thiazole derivatives of formula (I) - wherein R and R ¹ are the same or are different and use a 1: 10 to 1: 1 mixture of C 1-4 alkyl groups.

In the above formula, R and R ¹ are preferably methyl.

Copper oxyquinolate is a well-known antifungal agent (Phytophatology 36, 572 (1946)). The 5- (phenylcarbamoyl) -1,3-thiazole derivative of formula (I) and its fungicidal activity are disclosed in U.S. Pat. U.S. Pat.

Seeds of phytopathogenic fungi (e.g. Calonectria nivalis, Pyrenophora graminea, Tilletia caries, Ustilago avenae, Septoria nodorum, Telletia foetida, Ustilago hordei, Ustilago nigra, Uroaptis occulata, Pyrenophora avenae, Cochliobol) are used. However, these substances are toxic to warm-blooded animals. Other, less toxic substances are inappropriate because of their narrow spectrum of action.

The mixture used in the process of the invention is less toxic for seed dressing than mercury containing dressings and is suitable for field, horticultural and forestry use. The mixture may also be admixed with other known gonib control agents. The mixture may be admixed with one or more additional pesticides, such as insecticides (e.g., organic chlorine compounds such as lindane, organic phosphoric acid esters such as diazinon, isazophos and thiophanox, arm brown capsule, such as carbofuran, mercaptodimethyl, and bendiocarb) such as benzathrone, ciram and diphenylguanidine), thus protecting the seeds from pests such as insects and birds.

Compared to the use of conventional mercury-borne universal seed dressing agents, the mixture used in the process of the invention has a broader spectrum of action (e.g. in addition, it also has a synergistic effect.

The mixture used in the process of the invention is one or more carriers, for example talc, kaolin, bentonite. and barite minerals, tackifiers such as spindle oil, ethylene glycol, and polyvinylacetate. It may also contain pigments such as iron oxide and ruby toner.

The blend used in the process of the present invention may be formulated as a powder by mixing all solids, including the carrier and additives, until a homogeneous mixture is formed. The tackifier is then added and mixed again until the mixture is homogeneous.

In the case of liquid formulations, organic solvents such as xylene, dimethylformamide, ethylene glycol and methanol and cyclohexane are used as diluents, and surfactants (calcium calcododecylbenzenesulfonate, polyglycol ethers and arylpolyether alcohols) and dyes are used. (e.g., Rhodamine and methyl violet).

The weight ratio of the active ingredient of formula (1) to copper oxyquinolate is from 10: 1 to 1: 1, preferably from 1.25 to 7.5: 1, or more preferably from 1.25 to 3.75: 1.

The amount of active ingredient per 100 kg of seed according to the invention is as follows:

Copper oxyquinolate 5-50 g of the compound of formula I is 10-80 g

The following quantities are preferred:

Copper oxyquinolate 5-35 g of the compound of formula I is 35-50 g.

The process according to the invention is suitable, for example, for seed dressing of rye, wheat, barley and oats.

In the following example, seed treatment by Ehle, H., Forhbeyer, PE, Reinhard, H. and Roder, K. (1974). 3300 Braunschweig). In this example, the active ingredient of the formula I is 2,4-dimethyl-5- (N-phenylcarbamoylthiazole).

Example

Spring wheat (cv. Timmo) is artificially infected with the dry spores of Tilletia caries by adding 2 g of spores per kilogram of wheat seed. The contaminated seed is treated with different amounts of seed treatment agent. These wettable powder formulations are diluted with water and applied to the seed as a spray mist of liquid seed treatment agent de Vilbiss (brand name) by compressed air nebulizer based on the measured amount of seed and shaking the seed and chemical in a vessel for 5 minutes.

All formulations contain, in addition to the active ingredient, wetting and dispersing agents, pigments, choline and white oil.

HU 199062 Β

All formulations are diluted with water to maintain a constant application volume of 400 ml / 100 kg seed.

Seeds are sown outdoors on clayey loam soil, using the tractor-mounted seed drills of Oyjord. The plot size is 1.6 m x 5 m, four replicates, all treatments are done completely at random.

The prevalence of infection is estimated by examining 100 randomly selected strains per plot to determine the level of infection. The formulations and results are summarized in Table 1.

The results imply an increased efficacy of the compound of formula (I) when used in a mixture with resoxyquinolate, especially when the compound of general formula (I) is used in a lower concentration of the two. The results obtained with formulations 9, 10 and 11 are analyzed by comparing the results obtained with the compound of formula (T) alone or with copper oxyquinolate alone, and calculating the theoretical percentage protection obtained with a mixture of the compound of formula (I) and copper oxyquinolate.

It can be seen that the presence of copper oxyquinolate results in a synergistic increase in the efficacy of the compound of formula (I).

Table 1

PREPARATION (4) 1 2 3 4 5 6 7 8 9 10 11 (I). kepi. vegy.g 75 37.5 - - - 75 75 75 37.5 37.5 37.5 CuOQ (1), g - - 10 20 30 10 20 30 10 20 30 Protection X (2) 95.7 63.7 65.9 74.4 80.8 100 97.9 100 100 95.7 95.7 Theoretical protection X (3) - - - - - 98.5 98.9 99.2 87.6 90.7 93.0 (I) CuOQ (5) - - - 7.5 3.75 2.5 3.75 1,875 1.25

NOTES:

(1) Copper oxyquinolate (2) Detected mean X protection for 2 field experiments (3) Colby formula (4) Untreated control mean X at 47.5X infection.

(5) Weight ratio.

Claims (4)

PATENT CLAIMS A process for seed dressing against phytopathogenic fungi, characterized in that the seed is a 5- (phenylcarbamoyl) -1,3-thiazole derivative represented by the general formula (I) - in which R and R ¹ are independently A mixture of alkyl group and copper oxyquinolate in a weight ratio of 10: 1 to 1: 1 is seeded using 10-80 g of active ingredient of the formula I and 5-50 g of copper oxyquinolate per 100 kg of seed. 50 2. The process of claim 1, wherein the dressing is carried out with a mixture of the active ingredient of formula (I) and copper oxyquinolate in a weight ratio of 1.25 to 3.75: 1. Process according to claim 1 or 2, characterized in that 35 to 50 g of active ingredient of the formula I and 5 to 35 g of copper oxyquinolate are used per 100 kg of seed. 4. Process according to any one of claims 1 to 3, characterized in that the active ingredient of the formula (I) is 2,4-dimethyl-5- (N-phenylcarbamoyl) -1,3-thiazole.